Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
  • A61K8/73—Polysaccharides
  • A61K8/735—Mucopolysaccharides, e.g. hyaluronic acid; Derivatives thereof
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K31/00—Medicinal preparations containing organic active ingredients
  • A61K31/11—Aldehydes
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K31/00—Medicinal preparations containing organic active ingredients
  • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
  • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
  • A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K31/00—Medicinal preparations containing organic active ingredients
  • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
  • A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K31/00—Medicinal preparations containing organic active ingredients
  • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
  • A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
  • A61K31/726—Glycosaminoglycans, i.e. mucopolysaccharides
  • A61K31/727—Heparin; Heparan
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K31/00—Medicinal preparations containing organic active ingredients
  • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
  • A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
  • A61K31/726—Glycosaminoglycans, i.e. mucopolysaccharides
  • A61K31/728—Hyaluronic acid
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K31/00—Medicinal preparations containing organic active ingredients
  • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
  • A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
  • A61K31/737—Sulfated polysaccharides, e.g. chondroitin sulfate, dermatan sulfate
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
  • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/67—Vitamins
  • A61K8/678—Tocopherol, i.e. vitamin E
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
  • A61K8/73—Polysaccharides
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K9/00—Medicinal preparations characterised by special physical form
  • A61K9/0012—Galenical forms characterised by the site of application
  • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P17/00—Drugs for dermatological disorders
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P17/00—Drugs for dermatological disorders
  • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P17/00—Drugs for dermatological disorders
  • A61P17/16—Emollients or protectives, e.g. against radiation
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q19/00—Preparations for care of the skin
  • A61Q19/08—Anti-ageing preparations
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
  • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
  • A61K2800/59—Mixtures
  • A61K2800/592—Mixtures of compounds complementing their respective functions
  • A61K2800/5922—At least two compounds being classified in the same subclass of A61K8/18

Definitions

• the present invention relates to a new combination of a hyaluronic acid or a salt thereof and a low molecular weight sulphated polysaccharide; and the use of said combination in the fields of anti-aging and scarring.
• Hyaluronic acid is a molecule with a major role in the skin. This is indeed the main component of the extracellular matrix. The latter refers to the set of extracellular macromolecules of the connective tissue. It consists largely of glycoproteins, pure proteins and glycosaminoglycans.
• HA is a non-sulphated linear glycosaminoglycan composed of repeating units of disaccharides themselves composed of D-glucuronic acid and N-acetyl-D-glucosamine linked by alternating ⁇ 1-3 and ⁇ 1-4 glycosidic bonds between dimers ( Tammi R., Agren UM, Tuhkanen AL, Tammi M.
• ⁇ is a very high molecular weight polymer of between 600,000 and 3 MDa (BP: Hyaluronan Toole: From Extracellular Glue to Peracellular W: Nat Rev Cancer 2004, 4: 538-539).
• These low molecular weight sulfated polysaccharides have interesting biological properties: inhibition of collagen and elastin degradation, restructuring, anti-inflammatory action, and induction of HA production.
• wound healing is a complex and dynamic biological process that involves the interaction of many local and systemic factors in normal tissue repair.
• the progress of wound healing has three interrelated phases: hemostasis and inflammation, proliferation, and remodeling (Witte, MB, Barbul A. Surg Clin North Am., 1997 Jun; 77 (3): 509). -28.).
• Proliferation involves three observable processes: granulation, contraction and re-epithelialization.
• Macrophages are constantly releasing chemotactic factors and growth factors.
• Fibroblasts construct the new cell matrix necessary for cell growth at the bottom of the wound. This scaffold promotes cell migration.
• the endothelial cells trigger the formation of vascular buds that will form new capillaries, which will restore the perfusion and ensure the supply of oxygen and nutrients essential to the metabolic activity of cells in the wound.
• the contraction of the wound is a mechanism for reducing the size of the wound and the fibroblasts play a leading role in this contraction.
• Re-epithelialization is the regeneration of an epidemic that covers a wound to reform an effective barrier against the external environment, capable of to piggyback and regain its sensory and immune functions. It therefore involves the cellular processes of migration and proliferation of keratinocytes, but also the differentiation of this neoepithelium and the restoration of a basement membrane that reconnects the dermis and the epidermis.
• a wave of cellular mitosis occurs to fill the spaces left by the migration and provide cells for regenerating epithelial tissue. -dimensional.
• the proliferation steps of keratinocyte cells, fibroblasts or endothelial cells can be considered as one of the functional phenomena testifying to the healing activity of an active ingredient.
• An increase in the proliferation of fibroblasts would participate in the healing of a deep wound (damage to the dermis), whereas the increase in the proliferation of keratinocytes would participate in reepithelialization.
• the present invention relates to a combination comprising a hyaluronic acid or a salt thereof and a sulfated polysaccharide whose molecular weight is between 5 and 25 kDa.
• hyaluronic acid fragment of hyaluronic acid
• AH hyaluronan
• the combination comprises a hyaluronic acid or one of its salts whose weight average molecular weight (Mw) will be between 50,000 and 750,000 Da.
• the AH fragment or a salt thereof is characterized by a weight average molecular weight of between 60 and 120 kDa, said molecular mass being measured by an analytical method combining a Size Exclusion Chromatography (SEC) with a Multi-Angle Light Scattering Photometer (MALS) coupled to a viscometer (VIS) and a differential refractometer (RI).
• SEC Size Exclusion Chromatography
• MALS Multi-Angle Light Scattering Photometer
• VIS viscometer
• RI differential refractometer
• it will be sodium hyaluronate.
• the molecular weight of ⁇ or one of its salts can be measured using the European Pharmacopoeia method which measures the intrinsic viscosity with a Ubbelohde capillary viscometer (see European Pharmacopoeia 7.6, monograph of sodium hyaluronate ref .: 01/2011: 1472). This viscosity value is then related to the average molecular weight by the Mark-Houwink relationship. This method is long and requires perfect reproducibility.
• the weight average molecular weight of ⁇ or one of its salts is measured by the method SEC-MALS-VIS-RI which is an analytical method combining a size exclusion chromatography technique (Size Exclusion Chromatography - SEC) with a multi-angle light scattering photometer (MALS) coupled to a viscometer (VIS) and a differential refractometer.
• SEC-MALS-VIS-RI Size Exclusion Chromatography - SEC
• MALS multi-angle light scattering photometer
• VIS viscometer
• differential refractometer a differential refractometer
• the coupling of size exclusion chromatography SEC to an MALS detector allows after injection of a solution of polymers in a system chromatographically, separate these polymers by size in the chromatographic column, measure this size by light scattering and quantify them using a differential refractometer or a UV spectrometer.
• the hyaluronic acid or a salt thereof is solubilized in an aqueous solution of 0.1M NaCl and then eluted on a column filled with polystyrene-divinylbenzene beads of calibrated porosity. Large polymer chains do not pass through all pores and are therefore eluted before small chains.
• the MALS detector measures the scattering of incident light at different angles. These angles make it possible, by extrapolation, to measure R0, which is 0-angle scattering. R0 is directly proportional to the size of the molecule.
• the response Si of the differential refractometer is proportional to the total mass Ci of the polymer of degree of polymerization i according to the following equation (1):
• K ' is a constant related to the device
• the index of refraction index dn / dc is furthermore a specific polymer value studied.
• This ratio dn / dc can be measured according to the following protocol exemplified sodium hyaluronate. a / Apparatus and preparation of solutions:
• the measurements are made on a refractometer such as the Brice-Phoenix model having as incident light source a helium-neon laser
• the ratio dn / dc then corresponds to kx B where k represents the constant of the apparatus which is equal to 0.97.10 -5 in the present example.
• R0 K.Ci.Mi
• R0 is the diffusion angle RAYLEIG ratio
• Ci represents the total mass of polymer of degree of polymerization i [calculated according to equation (1)] of the injected solution
• Mi represents the molar mass of the desired polymer chain.
• the weight average molecular weight Mw can then be calculated according to the formula:
• Mw ⁇ CiMi / ⁇ Ci.
• Hyaluronic acid or its salt which is the subject of the present invention, may be obtained according to one of the processes known to those skilled in the art, such as those described in document EP1987153.
• HA is mainly obtained industrially by bacterial fermentation: the hyaluronic acid filaments are synthesized by bacteria.
• a high molecular weight native HA ranging generally from 1 MDa to 2 MDa is obtained by bacterial fermentation using a selected bacterial strain.
• the polymer obtained can then be separated from the bacterium.
• the solution is then purified and then hydrolysed by controlled acid hydrolysis until the desired molecular weight is obtained.
• the salt of hyaluronic acid will preferably be sodium hyaluronate.
• the low molecular weight sulphated polysaccharides may be chosen from sulphated fucans and sulphated ulvans with a molecular weight of between 5 and 25 kDa.
• Sulphated fucans are polysaccharides comprising sulfated L-fucose.
• These polysaccharides can be extracted in particular from brown algae, for example of the order Fucales or Laminariales.
• Sulphated ulvans are sulfated anionic polysaccharides comprising uronic acids (eg glucuronic acid, iduronic acid) and sulphates (eg 3-sulphate rhamnose, galactose, xylose, glucose) distributed in repeating units.
• uronic acids eg glucuronic acid, iduronic acid
• sulphates eg 3-sulphate rhamnose, galactose, xylose, glucose
• Type B ulvanobiuronic 3-sulphate consisting of 3-sulphate ⁇ -L-rhamnose bound to ⁇ -L-iduronic acid by a type 1 ⁇ 4 bond.
• Ulvans can be extracted in particular from green algae of the ulva type or enteromorph (Ulva sp., And Enteromorpha sp.).
• the sulphated fucan of low molecular weight is as described in WO 2010/086197.
• the sulphated ulvan of low molecular weight is as described in WO 2013/150253.
• the QT40® fraction marketed by Green Tech based on a particular oligosaccharide derived from the Ulva Lactuca algae: a sulpho-oligorhamnoglucuronan.
• the mass ratio of hyaluronic acid / polysaccharide is between 0.1 and 10.
• the mass ratio of hyaluronic acid / polysaccharide is between 0.5 and 5, and preferably between 0.5 and 2.
• the present invention further relates to a combination of hyaluronic acid or a salt thereof and low molecular weight sulphated polysaccharide according to the invention (i.e., of molecular weight between 5 and 25 kDa) for its use to promote the proliferation of fibroblasts.
• the present invention also relates to a cosmetic composition comprising, as an anti-aging active ingredient, a combination of a hyaluronic acid or a salt thereof and a sulphated polysaccharide with a molecular weight of between 5 and 25 kDa and further comprising at least one cosmetically acceptable excipient.
• the cosmetically acceptable excipients are suitable for topical administration.
• Acceptable excipients in particular ensure good stability, texture and a pleasant touch. It may also be for example formulating agents or additives of known and conventional use in cosmetics: mention may be made of surfactants, colorants, preservatives, perfumes, film-forming agents, thickeners, etc.
• the anti-aging compositions may be in the forms which are usually known for topical administration to the skin, that is to say in particular creams, emulsions, lotions, serums, masks, wrinkle-filler, eye contours,
• the object of the present invention is the cosmetic use of the combination according to the present invention or of this cosmetic composition according to the invention for combating the signs of cutaneous aging.
• the cosmetic use of the combination according to the present invention or the cosmetic composition according to the invention is more particularly intended to restore the material to the skin, strengthen its firmness and visibly reduce marked wrinkles and deep furrows.
• the present invention also relates to a method for combating the signs of cutaneous aging comprising the administration, preferably topically, of an effective amount of a combination according to the invention or of a cosmetic composition according to the invention to a person in need.
• Another subject of the present invention relates to a dermatological composition intended to accelerate cutaneous repair in order to restore the integrity and the quality of the skin
• a dermatological or cosmetic active ingredient the combination of a hyaluronic acid or one of its salts and a sulfated polysaccharide whose molecular weight is between 5 and 25 kDa above mentioned and further comprising at least one dermatologically or cosmetically acceptable excipient.
• composition is intended for topical application.
• the dermatologically (pharmaceutically) or cosmetically compatible excipients may be any excipient among those known to those skilled in the art in order to obtain a composition for topical application in the form of a milk, a cream or a cream. a balm, an oil, a lotion, a gel, a foaming gel, an ointment, a spray, etc.
• the composition will be in the form of a cream or ointment.
• the dermatological and cosmetic compositions according to the invention comprise at least one other active ingredient.
• This other active ingredient may in particular be selected from the group comprising anti-aging agents, healing agents, soothing agents, antipruritic agents, antioxidants, anti-radical agents, anti-UV agents, stimulating the synthesis of dermal macro-molecules or energy metabolism, moisturizers, depigmenting agents, antibacterial, antifungal, anti-inflammatory, or anesthetic.
• the compositions according to the invention which are preferably cosmetic, also comprise retinaldehyde.
• This complementary anti-aging active ingredient is a direct precursor of retinoic acid for a reactivating effect of immediate cellular metabolism. Retinaldehyde increases des receptor expression, CD44 and induces AH synthesis.
• composition according to the invention then comprises a combination of hyaluronic acid or a salt thereof, low molecular weight sulphated polysaccharide and retinaldehyde.
• hyaluronic acid or a salt thereof low molecular weight sulphated polysaccharide and retinaldehyde.
• Such an association has a restructuring and redensifying effect in the dermal-epidermal junction and the papillary dermis.
• the composition will further comprise a tocopherol derivative including the delta tocopheryl glucopyranoside: its powerful antioxidant effects protect the skin and maintain its luminosity.
• composition according to the invention then comprises a combination of hyaluronic acid or a salt thereof, low molecular weight sulphated polysaccharide and delta tocopheryl glucopyranoside.
• the other active ingredient will be chosen from healing agents, soothing agents and mixtures thereof.
• Such an active ingredient will preferably be used in dermatological compositions.
• another object of the present invention is a combination of hyaluronic acid or a salt thereof and low molecular weight sulphated polysaccharide or a dermatological composition containing it according to the invention for its use as a medicament (more particularly dermatological), especially for the treatment and healing of skin lesions.
• the present invention also relates to the use of a combination of a hyaluronic acid or a salt thereof and a sulphated polysaccharide of molecular weight between 5 and 25 kDa for the preparation of a medicament (more particularly dermatological), especially for the treatment and healing of skin lesions.
• the present invention also relates to a method for treating and healing skin lesions comprising administering, preferably topically, an effective amount of a combination of a hyaluronic acid or a salt thereof and a sulfated polysaccharide of molecular weight between 5 and 25 kDa or a dermatological composition containing it according to the invention to a person in need thereof.
• the dermatological and cosmetic compositions according to the invention are intended in particular for the care of injured skin:
• the treatment of lesions of the skin and mucous membranes according to the invention may in particular include the treatment of cuts, sutures, abrasions, scratches, scratches, scars post-surgery or post-act of cosmetic dermatology, superficial burns , sunburns.
• the present invention further relates to the use of a cosmetic composition according to the invention for improving healing and skin repair.
• Figure 1 shows the refractive index dn versus concentration c for sodium hyaluronate.
• Figure 2 shows the effect of AH according to the invention (HAF120) at 100 and 1000 ⁇ g / ml and Ascophyscient® at 10 and 100 ⁇ g / ml on the proliferation of fibroblasts. *: p ⁇ 0.05 and **: p ⁇ 0.01. Representative experience of 3 independent experiments.
• Figure 3 shows the effect of AH according to the invention (HAF120) at 100 ⁇ / ⁇ 1, Ascophyscient® at 10 ⁇ / ⁇ 1 and their association on the proliferation of fibroblasts. *: p ⁇ 0.05. Representative experience of 3 independent experiments.
• Figure 4 represents the effect of AH according to the invention (HAF120) at 1000 ⁇ / ⁇ 1, Ascophyscient® at 10 ⁇ g / ml and their association on the proliferation of fibroblasts. *: p ⁇ 0.05 and **: p ⁇ 0.01. Representative experience of 3 independent experiments.
• the technique used is that of the incorporation of a thymidine-like nucleotide, 5-bromo-2'-deoxyuridine (BrdU), into the DNA of S-phase cells at 37 ° C.
• This technique makes it possible to quantify the cells whose advance in the cell cycle is characteristic of a proliferative cell (S phase or DNA synthesis).
• FNH normal human fibroblasts
• DMEM Dulbecco's Modified Eagle Medium
• FCS fetal calf serum
• the cells are first deprived of FCS for 24 hours to stop the cell growth before incubating them in the presence of the molecules to be evaluated for 44 hours at 37 ° C., in a 5% CO 2 atmosphere.
• EGF epidermal growth factor
• Ascophyscient® induced the proliferation of fibroblasts in a very reproducible and statistically significant manner.
• the combination of Ascophyscient® with HAF120 induced the proliferation of fibroblasts in a synergistic manner.
• Ascophyscient® By inducing the proliferation of fibroblasts, Ascophyscient® and its combination with the 60-120 kDa fragment of sodium hyaluronate restores cellular metabolism and participates in dermal repair and the fight against aging.

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